91523-90-9

Upstream product

• 100-42-5 styrene 
• 524-38-9 N-hydroxyphthalimide 
• 41252-83-9 2-bromo-2-phenylethanol 

Downstream Products

• 93-56-1 phenylethane 1,2-diol 
• 91523-88-5 1-Phenyl-1,2-bis(aminooxy)ethane 

Relevant academic research and scientific papers

Metal-free three-component oxyazidation of alkenes with trimethylsilyl azide and N-hydroxyphthalimide

A novel and facile oxyazidation of alkenes under metal-free and mild conditions has been reported. A remarkable feature of the developed procedure is consecutive construction of C-O and C-N bonds in one step. The process allows quick and selective assembly of alkyl azide from readily available starting materials, where N-hydroxyphthalimide was used as an oxygen-radical precursor and TMSN3 as the N3 source. A range of aromatic alkenes bearing synthetically useful functional groups was tolerated.

Cobalt Catalyst-Controlled Selective Dioxygenation of Styrenes Using N-Hydroxyphthalimide with Molecular Oxygen

A cobalt-catalyzed selective dioxygenation of styrenes with N-hydroxyphthalimide (NHPI) was developed using molecular oxygen as the terminal oxidant. Alcohol and ketone products can be selectively formed from identical substrates by catalyst control. The reaction was applicable to a broad range of styrenes and exhibited good functional group tolerance. It provided a method for preparation of 1,2-diol or α-hydroxyketone derivatives. (Figure presented.).

Electrifying Phthalimide-N-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with N-Hydroxyphthalimide

An electrochemical process of free-radical difunctionalization of vinyl arenes with N-hydroxyphthalimide resulting in vicinal dioxyphthalimides was discovered. The reaction proceeds with the use of pyridinium perchlorate and pyridine as a supporting electrolyte and a base, respectively. The present approach involves the anodic generation of stabilized phthalimide-N-oxyl (PINO) radical, which adds to the carbon–carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical. A wide range of dioxyphthalimides were obtained in yields up to 81%.

Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide

Cerium(IV) ammonium nitrate was found to be a versatile reagent for the oxidative functionalization of styrenes using N-hydroxyphthalimide and iodine affording three different types of products with oxyphthalimide, nitrate and iodide groups. It was shown

Copper-catalyzed C–O coupling of styrenes with N-hydroxyphthalimide through dihydroxylamination reactions

An efficient method of copper-catalyzed 1,2-dihydroxylaminations of alkenes have been demonstrated under air conditions by using PhI(OAc)2as oxidant to furnish the dioxygenated products in 20–81% yields. This provided an alternative methodology to synthesis of dioxygenated products, which were easily transformed into diols under the reductive conditions. Furthermore, a free-radical addition mechanism was proposed in this transformation.

Oxidation of 1,2-Bis(hydroxylamines)

Oxidations of 1,2-bis(aminooxy)ethane (H2NOCH2CH2ONH2) and its phenyl substituted derivative (H2NOCHPhCH2ONH2) give a variety of products.Some are consistent with formation of the 1,4,2,3-dioxadiazene ring or a polymeric hyponitrite, while others derive from separate oxidation of the two ends of the hydroxylamine.Nitrogen yields are ca. 60percent in nickel peroxide oxidations and ca. 25percent in tert-butyl hypochlorite oxidations.